Fun with Fluorine: from Deoxytrifluoromethylation to para-Selective C-H Functionalization

Speaker

Ryan Altman
Associate Professor
Purdue University

Abstract

Simple O-based functional group (alcohols, ketones and aldehydes) remain amongst the most commonly exploited functional groups for synthetic transformations, and the extensive number of these motifs in natural products and pharmaceutically important building blocks provides a wide variety of potential substrates for transformations. In this area, we develop new reactions and synthetic sequences using decarboxylative strategies and fluorinated alkenes to convert simple O-based groups into biomedically significant fluorinated substructures. Further, we confirm that these methods streamline the syntheses of target molecules with appropriate physicochemical and biophysical properties and drug-like characteristics. Additionally, these explorations have revealed a new para-selective C–H functionalization reaction that enables access to medicinally relevant substructures from simple feedstock aromatic hydrocarbons, such as toluene.